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HIOC ATC code
N -[2-(5-Hydroxy-1H -indol-3-yl)ethyl]-2-oxo-3-piperidinecarboxamide
PubChem CID ChemSpider CompTox Dashboard (EPA ) Formula C 16 H 19 N 3 O 3 Molar mass 301.346 g·mol−1 3D model (JSmol )
c1cc2c(cc1O)c(c[nH]2)CCNC(=O)C3CCCNC3=O
InChI=1S/C16H19N3O3/c20-11-3-4-14-13(8-11)10(9-19-14)5-7-18-16(22)12-2-1-6-17-15(12)21/h3-4,8-9,12,19-20H,1-2,5-7H2,(H,17,21)(H,18,22)
Key:ZIMKJLALTRLXJO-UHFFFAOYSA-N
HIOC is a small-molecule agent which acts as a selective TrkB receptor agonist (active at at least 100 nM; prominent activation at 500 nM).[ 1] [ 2] [ 3] It was derived from N-acetylserotonin (NAS).[ 2] [ 3] [ 4] Relative to NAS, HIOC possesses greater potency and a longer half-life (~30 min or less for NAS in rats, while HIOC is still detectable up to 24 hours after administration to mice; ~4 hour half-life for HIOC in mouse brain tissues).[ 2] [ 3] It is described as producing long-lasting activation of the TrkB receptor and downstream signaling kinases associated with the receptor.[ 2] HIOC is systemically-active and is able to penetrate the blood-brain-barrier .[ 2] In animal studies , HIOC was found to robustly protect against glutamate -induced excitotoxicity , an action which was TrkB-dependent.[ 3]
A chemical synthesis of HIOC has been published in 2015.[ 5]
See also
References
^ Longo, Frank M.; Massa, Stephen M. (2013). "Small-molecule modulation of neurotrophin receptors: a strategy for the treatment of neurological disease". Nature Reviews Drug Discovery . 12 (7): 507–525. doi :10.1038/nrd4024 . ISSN 1474-1776 . PMID 23977697 .
^ a b c d e Iuvone, P. Michael; Boatright, Jeffrey H.; Tosini, Gianluca; Ye, Keqiang (2014). "N-Acetylserotonin: Circadian Activation of the BDNF Receptor and Neuroprotection in the Retina and Brain" . Advances in Experimental Medicine and Biology . 801 : 765–771. doi :10.1007/978-1-4614-3209-8_96 . ISSN 0065-2598 . PMC 4069859 . PMID 24664769 .
^ a b c d Shen, J.; Ghai, K.; Sompol, P.; Liu, X.; Cao, X.; Iuvone, P. M.; Ye, K. (2012). "N-acetyl serotonin derivatives as potent neuroprotectants for retinas" . Proceedings of the National Academy of Sciences . 109 (9): 3540–3545. doi :10.1073/pnas.1119201109 . ISSN 0027-8424 . PMC 3295250 . PMID 22331903 .
^ Tosini, G.; Ye, K.; Iuvone, P. M. (2012). "N-Acetylserotonin: Neuroprotection, Neurogenesis, and the Sleepy Brain" . The Neuroscientist . 18 (6): 645–653. doi :10.1177/1073858412446634 . ISSN 1073-8584 . PMC 3422380 . PMID 22585341 .
^ Setterholm NA, McDonald FE, Boatright JH, Iuvone PM (2015). "Gram-scale, chemoselective synthesis of N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-oxopiperidine-3-carboxamide (HIOC)" . Tetrahedron Lett . 56 (23): 3413–3415. doi :10.1016/j.tetlet.2015.01.167 . PMC 4445863 . PMID 26028783 .
Angiopoietin CNTF EGF (ErbB)
FGF
FGFR1 FGFR2
Agonists: Ersofermin
FGF (1 , 2 (bFGF) , 3 , 4 , 5 , 6 , 7 (KGF ), 8 , 9 , 10 (KGF2) , 17 , 18 , 22 )
Palifermin
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Selpercatinib
Sprifermin
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FGFR3 FGFR4 Unsorted
HGF (c-Met) IGF
LNGF (p75NTR ) PDGF RET (GFL)
SCF (c-Kit) TGFβ Trk
TrkA
Negative allosteric modulators: VM-902A
TrkB
Agonists: 3,7-DHF
3,7,8,2'-THF
4'-DMA-7,8-DHF
7,3'-DHF
7,8-DHF
7,8,2'-THF
7,8,3'-THF
Amitriptyline
BDNF
BNN-20
Deoxygedunin
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DMAQ-B1
HIOC
LM22A-4
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